Who is Jack Sheldon? You may remember him as Merv Griffin’s comedic trumpet-wielding sidekick, or the indelible voice on School House Rock, but musicians know him as a jazz giant. Unlike his close friend and collaborator, Chet Baker, Jack Sheldon survived the demons of drugs, alcohol and unspeakable personal tragedy. His signature sound continues to paint the landscape of American music. As friend Billy Crystal puts it, Jack Sheldon is “the last cat standing” from the bebop generation. Trying to Get Good features historic footage with Benny Goodman, Stan Kenton and other legends, on-camera interviews with Clint Eastwood, Billy Crystal, Merv Griffin, Chris Botti, Tierney Sutton, Johnny Mandel and many more, as well as never before seen performances with The Jack Sheldon Orchestra.

Trying to Get Good exposes Hollywood’s best kept secret - when the stars come out to play, it’s Jack Sheldon who plays for them. Trying to Get Good takes a look deep inside the eternally tormented soul of an artist who’s not just “trying to get good” on the trumpet, but in his life as well.